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EP 0678093 B1 2000-01-05 - 5-ALKOXY-1,2,4-TRIAZOLO[4,3-C]PYRIMIDINE-3(2H)-THIONE COMPOUNDS AND THEIR USE IN THE PREPARATION OF 5-ALKOXY-1,2,4-TRIAZOLO[1,5-C]PYRIMIDINE-2(3H)-THIONE AND 3-HYDROCARBYLTHIO-5-ALKOXY-1,2,4-TRIAZOLO[4,3-C]PYRIMIDINE COMPOUNDS

Title (en)

5-ALKOXY-1,2,4-TRIAZOLO[4,3-C]PYRIMIDINE-3(2H)-THIONE COMPOUNDS AND THEIR USE IN THE PREPARATION OF 5-ALKOXY-1,2,4-TRIAZOLO[1,5-C]PYRIMIDINE-2(3H)-THIONE AND 3-HYDROCARBYLTHIO-5-ALKOXY-1,2,4-TRIAZOLO[4,3-C]PYRIMIDINE COMPOUNDS

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US 9412488 W 19941031

US 14878993 A 19931105

Abstract (en)

[origin: WO9512595A1] 5-Alkoxy(1,2,4)triazolo(1,5-c)pyrimidine-2(3H)-thione compounds (I), such as 5-ethoxy-8-fluoro(1,2,4)triazolo(1,5-c)pyrimidine-2(3H)-thione, were prepared by treatment of a 5-alkoxy-1,2,4-triazolo(4,3-c)-pyrimidine-3(2H)-thione compound (II), such as 5-ethoxy-8-fluoro-1,2,4-triazolo-(4,3-c)pyrimidine-3(2H)-thione, with an alkali metal alkoxide in an alcohol solvent slected so that the 5-alkoxy group, the alkoxide, and the alcohol all have the same alkyl group. The trialkylammonium salts of the 5-alkoxy-1,2,4-triazolo(4,3-c)-pyrimidine-3(2H)-thione compounds were converted to 3-hydrocarbylthio-5-alkoxy-1,2-4-triazolo(4,3-c)pyrimidine compounds by reaction with a hydrocarbyl halide, such as benzyl chloride. The products are useful intermediates in the preparation of 5-alkoxy(1,2,4)triazolo(1,5-c)pyrimidine-2-sulfonamide herbicides.